77162-51-7

Basic information

• Product Name: R(-)-GAMMA-VINYL GABA
• Synonyms: R(-)-GAMMA-VINYL GABA;R(-)-V-VINYL GABA;r(-)-γ-vinyl gaba;ent-Vigabatrin;RMI 71894;(R)-4-aMinohex-5-enoic acid;5-Hexenoic acid, 4-aMino-, (4R)-
• CAS NO: 77162-51-7
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.158
• Product Categories: Linear Core Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives;Amines;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 77162-51-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 169-170 °C
• Boiling Point: 277.7°C at 760 mmHg
• Flash Point: 121.7°C
• Appearance: /
• Density: 1.064g/cm³
• Vapor Pressure: 0.0012mmHg at 25°C
• Refractive Index: 1.482
• CAS DataBase Reference: R(-)-GAMMA-VINYL GABA(CAS DataBase Reference)
• NIST Chemistry Reference: R(-)-GAMMA-VINYL GABA(77162-51-7)
• EPA Substance Registry System: R(-)-GAMMA-VINYL GABA(77162-51-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 77162-51-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 77162-51-7 differently. You can refer to the following data:
1. The R-enantiomer of Vigabatrin, a novel antiepileptic
2. The R-enantiomer of Vigabatrin, a novel antiepileptic drug. Antidepressant; antipsychotic; anxiolytic.

InChI:InChI=1/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1

Upstream product

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• 151929-39-4 ethyl (4S)-4-(benzyloxycarbonylamino)-6-methylthio-2-hexenoate 

Relevant articles and documents

Scalable Synthesis of Both Enantiomers of Vigabatrin, an Antiepileptic Drug

Vigabatrin is a potent inhibitor of gamma-aminobutyric acid (GABA) catabolism used for the treatment of epilepsy. Here we have synthesized both enantiomers of the drug vigabatrin in five steps from known intermediates using Wittig olefination and pyrolytic elimination as key steps. The target compounds are synthesized in gram scale amounts with >98 % enantiopurity.

Catalytic asymmetric intramolecular aminopalladation: Enantioselective synthesis of vinyl-substituted 2-oxazolidinones, 2-imidazolidinones, and 2-pyrrolidinones

A new catalytic asymmetric synthesis of five-membered nitrogen heterocycles is reported. This synthesis employs ferrocenyloxazoline palladacycles (FOP trifluoroacetate catalysts) 2 and 4 and proceeds by a catalytic cycle involving Pd(II) intermediates. Fo

Asymmetric Synthesis of Both Enantiomers of Vigabatrin: An Approach Using Methionine as the Chiral Pool

Both enantiomers of the potent GABA-T inhibitor, 4-amino-5-hexenoic acid (2), were prepared in five steps from (R)- or (S)-methionine using a one-pot reduction-homologation of an α-amino ester as the key reaction step.